Green’s Dictionary of Slang

headache n.

1. (orig. US) a problem, a cause of anxiety, a worry.

[US]C. Coe Hooch! 115: There’s too many headaches in that.
G.B. Gilbert Country Preacher 77: The new rectory was both beautiful and expensive, but it proved to be a great headache. It was more pretentious than my salary warranted.
[UK]S. Jackson Indiscreet Guide to Soho 57: The £5,000 a year executive and the smaller-income renter have plenty of headaches.
[Aus]D. Cusack Caddie 240: I began to have fewer headaches about money.
[US]‘Iceberg Slim’ Pimp 96: I won’t give you any headaches.
[Ire]W. Burrowes Riordans 93: Slurry disposal actually. It’s a fierce headache.
[US]N. Pileggi Wiseguy (2001) 122: He said I was making stuff up and that he had enough headaches without me driving him crazy.
[US]D. Hecht Skull Session 340: The Rizal thing was a major headache.
[UK]Indep. 10 Jan. 17: A millenial cash hangover is still causing headaches.
[US](con. 1973) C. Stella Johnny Porno 142: This my headache [...] I shouldn’t involve you.

2. (US) one’s husband or wife, boyfriend or girlfriend.

[US]Hecht & Fowler Great Magoo 25: That little headache of yours with the honky-tonk eyes is trouble — plenty.
[US](con. late 1920s) L. Hughes Little Ham III ii : He never was no headache of mine, baby.

3. a problematic individual.

[US]C. Stella Jimmy Bench-Press 33: I’m wondering they don’t put all the fuckups, the headaches like myself, in O.C. just to keep us quiet.

In compounds

headache-man (n.)

(US drugs) a Federal narcotics agent.

[US] cited by D. Maurer ‘Speech of the Narcotic Und.’ in Amer. Mercury Feb.
[US]Anslinger & Tompkins Traffic In Narcotics 310: headache man. A Federal agent investigating the drug traffic.
headache-stick (n.)

(US black) a stick used as a club, a police baton or truncheon.

Wkly Ariz Miner 11 jan. 2/1: A spot was found where blood and hair were plenty on the ground, and some headache sticks were found.
[US]St Paul Globe (Minn.) 7 Aug. 1/2: The maskinonge fishers carry a chunk of wood instead of a gaff-hook. They call it the headache stick, and when the lunge is alongside, down it comes on his flat skull .
[US]N.I. White Amer. Negro Folk-Songs 361: [reported from Durham, N.C., 1919] I want to century just one more time. / I don’t bother no man but the man with the headache stick.
[US]L. Berg Prison Nurse (1964) 57: You sure swing a mean ‘headache stick,’ don’t you, dep?
[US]L. Durst Jives of Dr. Hepcat (1989) 9: Hold your piechopper, don’t vip another vop or I’ll take my headache stick and massage your top. Up your frame and do about face and lead up on in to this sinful place.
M. Gwin Queen of Palmyra 218: It’s a headache stick [...] You don’t want to get in its way, or it’ll give you one bad-assed headache.